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Jill Schlesinger
You might even be able to get
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Jill Schlesinger
Welcome to the Jill on Money show. It's Friday, May 22nd and we are here answering financial questions for you. If you've got one, all you need to do is go to our website. That is jillonmoney.com jillonmoney.com, in the upper right hand corner, the there is a contact us button. When you click that button, a miracle happens. A form pops up. Mark, you are a miracle man because Mark made this all happen and you just write us a note and you ask a question. But what we found is it is a much better process for us to have you come on the air live with us. That way we can ask a lot of follow up questions that are so nosy and, you know, you can change your name if you want to. It's fine. So I encourage people to come on the program. It seems like a richer experience and it really works out great. Don't forget while you're on the website, we've got all sorts of fun stuff there. We have other broadcasts. We have a new show or a rebranded show. Our Money Watch show is turning into Money Moves. There's going to be a video component. You're going to want to make sure that you subscribe to our Money Watch podcast. I don't know, Mark. By the time this airs, it might be that we have a whole new slate ready with Money Moves right there at the bottom. You know what also is happening today, Mark?
Mark Teo
The end of radio.
Jill Schlesinger
It's sad. Is it? I don't know, it's a little sad. So Mark and I come from the world of radio and we met through the CBS radio network and it's shutting down today. So if you want to listen to our final radio show, which is like 790 or 791, I think I might have made an incorrect count, Mark. I think I said it was 790 on the last show, but I think it's actually 791. All right, fine. We've been doing it for 15 years. This is the show that we won lots of awards for. It's really the basis of the show you're listening to right now. So if you want to listen to that show, you can go to our YouTube channel, which is Jill on Money, or just go to the website jillonmoney.com and click the radio link and you'll see this weekend will be our last broadcast. Do you feel winsome about that, Mark?
Mark Teo
It sounds weird, but no, I really don't. Not at all. And I think I said this on the final show. That's because we have the podcast. If we didn't have the podcast and this was the end of everything, it'd be a different story.
Jill Schlesinger
We're so grateful for everyone at radio because they actually allowed this show to really take hold. I think that without the radio show, we could not have really been in a place to launch this show, do this show the way we wanted to do it and bring it to the place where it is right now. So with the help of CBS Radio as well as all of you guys, it has been a thrilling ride. Yeah, Mark, it's sad because we only had four Gracie Awards. You have two and I have two. But maybe that was the way the universe wanted it to.
Mark Teo
We're going to get some more for the podcast. Don't worry.
Jill Schlesinger
Oh, all right, good, Mark. Going crazy with going through awards season. All right, let's get to you. Enough about us. Let's talk to Vinnie. He joins us from Massachusetts. Vinnie, how are you? And what can we do for you today?
Vinnie (Caller)
Good morning, guys.
Jill Schlesinger
What's happening, man?
Vinnie (Caller)
Well, I'm nearing retirement. I'm 63 years old and I've been saving since my 20s and in various different accounts. So I got my money spread out all over the place. And so I see a lot of, like, things on YouTube about taxes and this and that. And I think I might have made a mistake because I never converted to a Roth or started a Roth and whatever. I don't know if it's too late.
Jill Schlesinger
Listen, for first of all, you are where you are. So what if you made a mistake? I made a million mistakes in my life.
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Jill Schlesinger
It's all right. Let's figure it out. So you're 63. Are you married? Single. What do you got?
Vinnie (Caller)
I'm married with one child.
Jill Schlesinger
Okay. How old's your spouse?
Vinnie (Caller)
She is 56.
Jill Schlesinger
Okay. She's still working.
Vinnie (Caller)
Well, we have a small business, so she actually works with me about four hours a day.
Jill Schlesinger
Okay. And how old's the kid? Grown?
Vinnie (Caller)
Yeah.
Jill Schlesinger
19. Whoa. Yes, 19. Well, you got a late start, brother.
Vinnie (Caller)
Yeah, they think. They think I'm his grandfather. I sure did.
Jill Schlesinger
Oh, my God. You better stay fit because nobody wants to be like the grandpa in college or working or what. What's 19 year old doing?
Vinnie (Caller)
He just started college, finish finishing up his first semester.
Jill Schlesinger
How's it going?
Vinnie (Caller)
Great. He's a smart kid.
Jill Schlesinger
Okay, good. How you paying for college?
Vinnie (Caller)
Well, right now, luckily, it's free. Oh, the community college. I do have a 529, but it's not that much in it, but I do have some. About 10,000.
Jill Schlesinger
Great. So community college is free for two years and then you see what happens next. Or do you think, like, transfer to state school? What do you think's likely?
Vinnie (Caller)
Definitely going to transfer. I want him to stay in school.
Jill Schlesinger
Okay.
Vinnie (Caller)
And I think he does too. He likes it.
Jill Schlesinger
Great. That's amazing. Vinnie, how much do you earn right now?
Vinnie (Caller)
Oh, it's a straight commission, so, you know, I can't really. I can think of an average. It's anywhere between 80 to like maybe a hundred thousand a year depending.
Jill Schlesinger
Okay. And your wife adds about how much to that?
Vinnie (Caller)
I would say about 20.
Jill Schlesinger
Okay. How's your cash flow based on the income you have?
Vinnie (Caller)
It's. It's so tight, Jill, because I put so much away.
Jill Schlesinger
Oh, okay.
Vinnie (Caller)
I kind of do it to myself. I know, but.
Jill Schlesinger
All right, but that's, like, different than, like, oh, my God, I can't pay for electricity. So. So let's find out what. All right, so let's start with what kind of retirement plan do you have?
Vinnie (Caller)
I started a 401k. So I pay myself about every two weeks. About 2000 a week.
Jill Schlesinger
Okay.
Vinnie (Caller)
And then I put away about 13 to 1400. And then I match myself.
Jill Schlesinger
Oh, wow.
Vinnie (Caller)
3%. Oh, I know.
Jill Schlesinger
All right, how much is in the 401k right now?
Vinnie (Caller)
That one. I had just started it because Vanguard stopped doing 401ks a couple years ago.
Jill Schlesinger
Yeah.
Vinnie (Caller)
So what I did is I transferred that money to my regular IRA with Vanguard, and I started a new one with this other company, and it's got about 27,000 in it right now.
Jill Schlesinger
All right, how much does the IRA have in it?
Vinnie (Caller)
I have so many, Joe, so.
Jill Schlesinger
Oh, my God.
Vinnie (Caller)
I know. So I have one here with 402,000.
Jill Schlesinger
Okay, keep going. I'm writing it down.
Vinnie (Caller)
Okay. And then I. I did one for my wife.
Jill Schlesinger
Okay.
Vinnie (Caller)
Because I can't contribute because my account said that I make too much, and you want to be tax deductible. So anyway, I started one for her, and she's got about 48,000.
Jill Schlesinger
What else?
Vinnie (Caller)
In the other. The other fund I have. They're all different, various funds. I've got an equity income fund with 117,000.
Jill Schlesinger
Wait a minute. Is this a retirement account or just like.
Vinnie (Caller)
Okay, these are retirement.
Jill Schlesinger
So in addition to the 402, in addition to the 48,000, there's 117 in another IRA account?
Vinnie (Caller)
Yes.
Jill Schlesinger
Okay.
Vinnie (Caller)
Another one.
Jill Schlesinger
Can't stop, can you?
Vinnie (Caller)
I just kept opening them up because.
Jill Schlesinger
Geez Louise. Okay, what's the next one?
Vinnie (Caller)
This is the big one.458,000.
Jill Schlesinger
Where's that held?
Vinnie (Caller)
That's held at a. In a fund called Ultra at American Century.
Jill Schlesinger
Oh, did you have a broker at some point?
Vinnie (Caller)
No, I just back in my 20s, it said, if you have 10,000 in this fund, you'll be a millionaire.
Jill Schlesinger
And, you know, well, they were close. You got a half a million. All right, American century ultra, the 117, 48, 402. What else? Keep going, man. The news just keeps getting better.
Vinnie (Caller)
Ah, yes. And then I do have. Once I hit a certain amount in American Century, they Set me up with a private client group.
Jill Schlesinger
Yeah.
Vinnie (Caller)
And they made me sell some of the Ultra, and so I transferred that to them. And there's160,000 in that fund.
Jill Schlesinger
160,000 in just another fund.
Vinnie (Caller)
Yeah, that's the. That's managed by the managed.
Jill Schlesinger
That's a managed account. Okay. How much they charge you for that?
Vinnie (Caller)
I think. Well, they say. They.
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They take.
Vinnie (Caller)
They. They charge me, then they take it back, but I think it's like 1%.
Jill Schlesinger
Okay, we're gonna clean this up. Don't you worry. Okay, so I'm adding up a lot of numbers here. What else?
Vinnie (Caller)
And then. Then I have another fund in American Century that's not in an IRA. I just.
Jill Schlesinger
Taxable.
Vinnie (Caller)
Yeah.
Jill Schlesinger
Yeah.
Vinnie (Caller)
So that's. That's got 166,000.
Jill Schlesinger
Next.
Vinnie (Caller)
Then again, in American Century, it's just a money market. Not much in it. 1600.
Jill Schlesinger
Okay. What about money in the bank?
Vinnie (Caller)
Okay, here we go. Altogether?
Jill Schlesinger
Yeah.
Vinnie (Caller)
282,000.
Jill Schlesinger
Okay. That's a nice cushion.
Vinnie (Caller)
Yeah. 250 of it, though, is in a. In a CD. Mm. And I get the interest paid to me monthly because I kind of use that as a buffer if I'm having a bad month.
Jill Schlesinger
Yeah, because you're such a variable. Income from the commission. Yeah, I got you. Okay, let's keep going here. Do you own your own home?
Vinnie (Caller)
Yes.
Jill Schlesinger
What do you think it's worth? I don't.
Vinnie (Caller)
I'm going to. I'm going to say about 350.
Jill Schlesinger
And do you have a mortgage on it?
Vinnie (Caller)
No.
Jill Schlesinger
Do you have any plans to move?
Vinnie (Caller)
Not. Not presently, no.
Jill Schlesinger
So what are you thinking really, about retirement?
Vinnie (Caller)
Joe, I've been doing this for 20 years, and it's getting to me. It's physically demanding, mentally draining, and I like to retire at 65, but maybe just step away from this and then just look for something else. Part time.
Jill Schlesinger
Okay.
Vinnie (Caller)
Yeah. I'm averaging, you know, 65 to 70 hours a week. And I hate to admit it, but 20 years, no vacation, Jill. Six days a week. Yeah. I was just always afraid. I was always afraid. And even at this day, I'm afraid to spend money. And I just. Like I said, I always feel like I'm broke.
Jill Schlesinger
All right.
Mark Teo
Guarantee you he could probably retire before that if he wanted to, because he doesn't.
Jill Schlesinger
That's what I'm thinking. How much money do you think you spend on a monthly basis?
Vinnie (Caller)
Well, you know, the biggest cost for me, guys, right now is my health insurance. It's 2,000amonth. So I thank goodness That I don't have a mortgage, because if I had that, and with the prices of everything going up, I honestly don't think I could afford it.
Jill Schlesinger
I mean, I think you guys, you could, but. All right. Healthcare is to 6,000amonth.
Vinnie (Caller)
Yeah.
Jill Schlesinger
All right. Have you ever gone and looked at your Social Security benefit? Okay.
Vinnie (Caller)
Yes.
Jill Schlesinger
So let's talk about that. What is the Social Security benefit at? 67. And what is it at 70?
Vinnie (Caller)
Okay, 67. It's yearly. 30,000. 5.
Jill Schlesinger
28. 30,528. Yep. 70.
Vinnie (Caller)
70 would be 38. 3. 16.
Jill Schlesinger
And I imagine your wife would claim half of yours, right?
Vinnie (Caller)
I. I guess we. We haven't really.
Jill Schlesinger
Because I think that she probably doesn't have as much income. So I'm guessing that's the case, right?
Vinnie (Caller)
No, that's true.
Jill Schlesinger
That's right. Okay. All right. How are we going to get you to spend money? Okay? You have plenty of money. Okay, you listening to me? Do you hear this? How can we get them to spend. How can we do this? Because I feel like I. I think that anyone running the numbers can objectively say that you have 4, 8, 9. You have more like $1.2 million.
Mark Teo
It's hard to see it, though, when it's in a zillion different places.
Jill Schlesinger
Yes.
Vinnie (Caller)
I got two other places I didn't talk to you about. Oh, what now?
Jill Schlesinger
Tell me more.
Vinnie (Caller)
So. So. I'm so sorry, you guys. So Fidelity. I have another $21,700.
Jill Schlesinger
Okay.
Vinnie (Caller)
And then Robin Hood. It's just kind of like, you know, it's my version of going to the casino.
Jill Schlesinger
Yeah. Yeah.
Vinnie (Caller)
It's like 5,000.
Jill Schlesinger
All right.
Vinnie (Caller)
And then I have vaulted, which I buy gold and silver. I just started that.
Jill Schlesinger
That's gonna stop doing that. Okay, fine. How much is in there?
Vinnie (Caller)
3,000.
Jill Schlesinger
All right. I'm not including those. Let's just leave that aside.
Vinnie (Caller)
Okay?
Jill Schlesinger
It's fine. Okay. All right. So. 459. A million 1.1. There's. So, Mark, I did quick calculation. Looks like 1.2 in retirement.
Mark Teo
Yeah, I got, like, 1.6 total.
Jill Schlesinger
Yeah. Okay. Okay. So I'm not even including the bank account. You know, this is a weird thing to say, but is there a world in which we could get you to slow down? Like, in two years, just, you know, slow down? And then what I think would make sense is, in advance of that, you've got a big task ahead of you. You need to consolidate these accounts. Because if you knew that you had $1.2 million and you knew that we could just pull out a chunk of money every single year or every single. It's probably going to be better monthly for him, don't you think, Mark? That like, we set up an automatic monthly draft.
Mark Teo
Yes.
Jill Schlesinger
So here's how it would go. You can work with the people at American Century or you can do this yourself. But what you should say to the folks at American Century is, I need to consolidate all of my accounts. Now. Do you like Vanguard? Is that like your preferred place?
Vinnie (Caller)
Well, Vanguard is when I started to learn about the index funds. So that's when, you know, I got a late start, but that's when I started doing, you know, with them.
Jill Schlesinger
Do you feel like, where do you feel most comfortable? That's what I want to know.
Vinnie (Caller)
Vanguard is kind of like DYI because no one ever reaches out to me except, you know, American Century. She actually calls me once a year.
Jill Schlesinger
Well, I'm sure she does with your 1% charge.
Vinnie (Caller)
Yeah, I guess so.
Jill Schlesinger
I mean, you can get. Okay, here's your choices. I'm going to get. So I can't do this for you, but what I can tell you is, objectively, you have plenty of money. I think your game plan should be that you figure out where you can consolidate these accounts. Now, you could easily do this at Vanguard. What you would do is right now you have that Vanguard account with like. Is that the 400,000 at Vanguard? The 402, yeah.
Vinnie (Caller)
Altogether 455.
Jill Schlesinger
Right. Okay. You go onto the website or you call the 800 number and you say to them, I want to use Vanguard Personal Service Advisor. It's like what you're getting at American Century, but it is a third of 1%.30. I think that's the fee still. So it's cheaper and someone will take care of you. Then you say to this person, I'm going to send you all of my statements. I need to consolidate these accounts. I want one IRA account for myself and one IRA account for my wife. That's all. And then, of course, you could have the taxable account as well. Or you do it the other way. You say to American Century, I want to consolidate everything here. I want you to bring everything in. I want you to not just manage my money. I want to do full blown financial planning. I want you to set me up so I can get monthly income distributed from my retirement account. And I want you to make sure that you run these numbers so that I feel comfortable that I'm not going to run out of money. You will take the amount of money that, you know, you say like. Again, like, we're not really sure exactly how much you need, but let's just say $6,000 a month, you will then probably take. I'm just going to give you a round number, about 100 grand a year out of that fund, out of that retirement account. You'll divide it by 12, it'll come out. I'm taking 100, even though you only need the six grand a month, because I want to account for the fact you got to pay tax on the money. Right. So we're going to pull the money out of the account. So you again, if you did. If you started it this year at 63, 64, 65, 66, 60. I know you won't allow this because you're probably not going to let yourself retire before 65. So let's just say 65, 66, 67. Those three years, you're going to pull 300 grand out. You're going to pay the tax on it. No big deal. You have to get the money out anyway. The IRS is going to force that. Then you're going to claim your Social Security. Then you're going to reduce the amount you're taking from your retirement accounts, probably by about half, I would assume. And then you're going to keep doing it. You're going to live your life. And you've got to give yourself permission to pull the money out, though, Vinnie, you're going to drive yourself crazy. And by the way, if you don't pull the money out and right now, between, say, 65 and 75, you're going to get killed because you're going have to pay. You have to take this money out anyway. You might as well take it out when you need it. You won't need as much once you're. Once you claim Social Security and then your wife claims Social Security, you won't need as much.
Vinnie (Caller)
Mm.
Jill Schlesinger
And you got plenty of money. You can make this work.
Vinnie (Caller)
So start claiming at 67, do you
Jill Schlesinger
think, or should I wait till. Let me ask you a question. How's your health? For real?
Vinnie (Caller)
It's okay. You know, it's minor aches and pains, arthritis. That's pretty much it.
Jill Schlesinger
But nothing. Nothing serious. I mean, if you could wait till 70, it would be great. Yeah. Mark, do you have an opinion about 60? I kind of want to make him go. I would love it to be 67 because I want you to have some cash flow. But it's better to wait till 70, obviously. But, you know, what do you think, Mark?
Mark Teo
The numbers are obviously better at 70, but, you know, I. As long as somebody at least waits to 67, then I'm fine.
Jill Schlesinger
Yeah. Okay, so 67 is the bottom line. And if you want to wait longer, fine. But don't be working more and kill yourself to get yourself to 67 or 70. Yeah, you. You deserve to do this, man.
Vinnie (Caller)
I know.
Jill Schlesinger
You know, you really do. It's okay. It's just. Okay.
Mark Teo
Hear it in the voice, you know?
Vinnie (Caller)
You know, I. I just grew up in a family that struggled, and, you know, I saw what my parents went through, and I just. You know what I mean? It just.
Jill Schlesinger
Yes.
Vinnie (Caller)
Every time I spend any money, I just feel so guilty, and I. And I have to think about it for, like, an hour. Do I really need this? You know, it's just.
Jill Schlesinger
It's just
Mark Teo
even, you know, you're saving to eventually spend it.
Vinnie (Caller)
Yeah.
Jill Schlesinger
That's the whole point. And in fact, you know what? You say you're living a little bit tight right now. Stop saving so much. Stop. Just stop. Don't worry about it.
Mark Teo
You have what you need.
Jill Schlesinger
You have what you need. So pull back. Spend a little.
Vinnie (Caller)
Live a little.
Jill Schlesinger
You really can. I don't know, like, look, I can't do this work for you.
Vinnie (Caller)
No, no, I get it.
Jill Schlesinger
I really. I feel so confident that you can do this. You've worked so hard to get here. I wish that I could, like, make it. I wish I could wave my magic wand and allow you to do it. But one of the ways that this can work is that if you set this up as an automatic payment, I think that's how it would work best for you. Because I don't think if we rely on you to just pull the money out in the beginning of the year, I think you're going to say, oh, my God, the market's down. You really should set this up as a monthly distribution. And if you do it at Vanguard, that's fine. If you do it at America's entry, it's fine. What did you say, Mark? I'm sorry.
Mark Teo
And consolidate. It's just when you have everything scattered all over the place, it's. It's hard to actually see that you have what you need.
Jill Schlesinger
Exactly.
Vinnie (Caller)
I tell you what. You know, this. This little homework you guys gave me, you know, write everything down, but just by writing it down, it became more crystallized.
Jill Schlesinger
Yes.
Vinnie (Caller)
And I started saying, holy crap, I'm using a lot of ink here, and I shouldn't have to do that, you know? Yeah.
Jill Schlesinger
And you do it, and you're doing great. So you and your wife have done an amazing job. Let me ask you a question, because you have a 19 year old. You guys have a will. Do you have your estate documents done?
Vinnie (Caller)
No. No.
Jill Schlesinger
All right. I know you got to do that only. Okay. The kid. Okay. Let's just say God forbid you and your wife are driving together, you're in Massachusetts. So let me just make it clear. The Mass. Holes out there on the road and something happened to the both of you, your kid would inherit a lot of money, Right? Who's going to help with that? You got to think about this, right? And who would take care. I mean, this kid's in college. He needs someone to be like a guardian still to, like, the age of majority, which I think In Massachusetts is 21 or 23. But, you know, you should. You got to think about this. Do you have a sibling? Do you or your wife have siblings around?
Vinnie (Caller)
Yes, my wife has a sister and I have two sisters. Does.
Jill Schlesinger
Would you say that one of those three people would be more inclined to help or be better at.
Vinnie (Caller)
I think any of them, yeah.
Jill Schlesinger
All right. You and your wife need to have that conversation. You really do. Okay. I'm sorry. It's like a. I don't want to. I certainly don't want to end on a bummer. You're in great shape. Get your estate planning done. How's that?
Vinnie (Caller)
Okay.
Jill Schlesinger
Is that good?
Vinnie (Caller)
Sounds good.
Jill Schlesinger
Stay in touch with us. Let us know how the consolidation goes. Mark, you're gonna. We're gonna follow up with him, gang. Mark makes such a good point that, you know, when you actually see everything in one place, it can be. It can actually help you get to the conclusion that I think that we all knew, which is as Vinnie's telling us the story, and he keeps adding an account, an account and account and account. We knew this guy's a super duper saver, he and his wife. So this is a good reminder for all of us that, you know, it's wonderful to save. It's great to get consolidation before retirement occurs. And it's also really smart to be able to think about ways to plan how you're going to receive the money that you worked so hard to save. Right? It's not there to just sit there. It's there so that you can live and enjoy your life. So hopefully you all got that message.
Vinnie (Caller)
So.
Jill Schlesinger
So if you're like, Vinny got accounts all over the place, if you are thinking about whether or not the next step for you is managing your money yourself or whether you should have someone else do it. Get in touch with us. Go to jillonmoney.com click the contact us button, write us a note, and if you want to join us on the air, just check the box. Don't forget to subscribe to our free weekly newsletter, which comes out today Fridays, and that will also get you our blog. You can subscribe to us on the Odysee app or wherever you find your favorite place. Podcasts Our music is composed by Joel Goodman. Mark Teo is our executive producer and king of all things web. We are distributed by the lovely folks at Odyssey. Please lift someone up. Change your work, Change your wealth, Change your life. Thank you for listening and we'll talk to you on Monday.
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Jill Schlesinger
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Episode: Tired but Afraid to Retire and Spend
Date: May 22, 2026
Host: Jill Schlesinger, CFP®
Producer/Co-host: Mark Teo
Caller: Vinnie from Massachusetts
In this episode, Jill and Mark take a call from Vinnie, a 63-year-old self-employed business owner struggling with retirement anxiety despite diligent lifetime saving. Vinnie is financially “tired but afraid to retire and spend,” overwhelmed by scattered accounts and guilt about using his hard-earned money. The conversation centers on helping Vinnie consolidate his resources, develop confidence in his retirement plan, and overcome psychological hurdles to enjoying his savings.
"Every time I spend any money, I just feel so guilty, and I have to think about it for, like, an hour. Do I really need this?" – Vinnie (19:21)
Lifestyle: Works 65–70 hours/week, no vacation in 20 years (11:12).
Health Costs: $2,000/month for health insurance, biggest worry in retirement (11:37).
"Don’t be working more and kill yourself to get yourself to 67 or 70. You deserve to do this, man." – Jill (18:53)
"When you have everything scattered all over the place, it's hard to actually see that you have what you need." – Mark (20:32)
"Set this up as an automatic payment... you should set this up as a monthly distribution. And if you do it at Vanguard, that's fine. If you do it at American Century, it's fine." – Jill (19:56)
"Stop saving so much. Stop. Just stop. Don’t worry about it. You have what you need. Pull back. Spend a little." – Jill ([19:33]–19:45)
"It's not there to just sit there. It's there so that you can live and enjoy your life. So hopefully you all got that message." – Jill (22:55)
"Just by writing it down, it became more crystallized. And I started saying, holy crap, I’m using a lot of ink here, and I shouldn't have to do that!" – Vinnie (20:40)
On making “mistakes” not converting to Roth:
"You are where you are. So what if you made a mistake? I made a million mistakes in my life... It's all right. Let's figure it out." – Jill (05:30)
On Vinnie's runaway account creation:
"Can't stop, can you?" – Jill (08:48)
On withdrawal anxiety:
"How are we going to get you to spend money?... Because anyone running the numbers can objectively say...you have more like $1.2 million." – Jill (12:28)
On the need to slow down:
"Is there a world in which we could get you to slow down?" – Jill (13:49)
On family financial anxieties:
"I just grew up in a family that struggled, and...every time I spend any money, I just feel so guilty..." – Vinnie (19:14)
On estate planning caution:
"Let me just make it clear... something happened to the both of you, your kid would inherit a lot of money. Who's going to help with that?" – Jill (21:03)
| Timestamp | Segment / Key Topic | |-----------|------------------------------------------------------------------| | 05:01 | Vinnie introduces his concern about disorganized finances & Roth | | 07:08 | Admits to tight cash flow due to over-saving | | 08:05 | Detailed breakdown of scattered retirement accounts | | 10:16 | Reports substantial cash savings / CD buffer | | 10:40 | Home owned outright, $350k value | | 11:12 | Describes work exhaustion, never taking vacations | | 12:07 | Social Security benefit discussion | | 13:49 | Jill/Mark calculate net worth, recommend slowing down | | 16:02 | Explains withdrawal and tax strategy | | 18:46 | Social Security timing debate | | 19:14 | Vinnie’s emotions and inherited money anxieties emerge | | 20:32 | Mark stresses account consolidation for clarity | | 21:01 | Jill strongly urges estate planning | | 22:55 | Final reminders: Save for spending, not just for saving |
Jill and Mark’s compassionate, plain-spoken advice guides Vinnie (and listeners) through both the math and emotion of retirement. This episode is a must-listen for super-savers who struggle to switch from growing their nest egg to confidently drawing it down and enjoying their hard work.
"Change your work, change your wealth, change your life." – Jill
Resource: If you need similar retirement or personal finance help, visit jillonmoney.com and click “Contact Us.”